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Ergocornine

HCID 73453
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Basic information

CAS
564-36-3
Standard SMILES
CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](NC(=O)[C@@H]3C=C4c5cccc6[nH]cc(c56)C[C@H]4N(C)C3)(C(C)C)C(=O)N12
InChIKey
UJYGDMFEEDNVBF-OGGGUQDZSA-N
Molecular formula
C31H39N5O5
Average molar mass
561.7 g/mol
Monoisotopic mass
561.29511936

Overview

Ergocornine is ergotaman bearing a hydroxy group at the 12' position, isopropyl groups at the 2' and 5'alpha positions, and oxo groups at positions 3', 6', and 18. It is a natural ergot alkaloid. It derives from a hydride of an ergotaman.

Names & identifiers

Preferred name
Ergocornine
IUPAC
(6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-di(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
English name
ERGOCORNINE
Molecular formula
C31H39N5O5
Molecular weight
561.67

Names & synonyms

Ergocornine564-36-3ErgocorninCHEBI:48207W36B25464DTXSID4097184112'-hydroxy-3',6',18-trioxo-2',5'alpha-di(propan-2-yl)ergotaman12'-Hydroxy-2',5'-alpha-bis(1-methylethyl)ergotaman-3',6',18-trioneNSC-407316ergocorine mesylate(6aR,9R)-N-((1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-di(propan-2-yl)-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamide(6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-di(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
Show more names
NSC 407316Ergot CornynERGOCORNINE USP/EP/BPERGOCORNINE >95% DOPAMINE RECEPTOR AGO12'-Hydroxy-2',5'α-diisopropylergotaman-3',6',18-trione12′-Hydroxy-2′,5′-α-bis(1-methyl-ethyl)ergotaman-3′,6′,18-trion12′-Hydroxy-2′,5′-α-bis(1-methyl-ethyl)ergotaman-3′,6′,18-trione

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
118 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
6
Rotatable bonds
4
Heavy atoms
41
Formal charge
0
Complexity
1,170

Physicochemical properties

Melting point
182 · 182-184℃ (decomposition) (methanol )
alpha
20 · D20 -110° (pyridine); -175° (chloroform)
Boiling point
628.48 °C · 628.48°C (rough estimate)
Density
1.1897 · 1.1897 (rough estimate)
refractive index
1.75 · 1.7500 (estimate)
solubility
45 % · 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.4 mg/mL
form
solid
pka
9.58 · 9.58±0.60(Predicted)
color
white
CAS DataBase Reference
564 · 564-36-3
FDA UNII
7 W36B25464 · 7W36B25464
RIDADR
1544 · UN 1544 6.1/PG 3
WGK Germany
3 · 3
RTECS
7630000 · KE7630000
HazardClass
6.1 · 6.1(b)
PackingGroup
III

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (L1921)

Health EffectsIngestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 item

Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Ergometrine is also known to have a non-receptor specific oxytocic activity. (A2914, A2915, A2916)

Signs and Symptoms · 1 item

Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (L1920)

Chemistry & industry

Uses & manufacturing

Uses · 1 item

Ergocornine is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. Ergocornine is one of 3 similar peptides referred to as ergotoxine alkaloids, the other two being ergocryptine and ergocristine. Ergotoxines prepared into their hihydroergotoxine mesylates, commonly known as ergoloid mesylates, are used in the symptomatic therapy of age-related dementia. (L1918, A2915)

Applications

UsesErgocornine is a natural ergot alkaloid derived from lysergic acid. Ergocornine is a component of Ergotoxine. Ergocornine is isolated from Ergot.

Additional notes

DefinitionChEBI: Ergotaman bearing a hydroxy group at the 12' position, isopropyl groups at the 2' and 5'alpha positions, and oxo groups at positions 3', 6', and 18. It is a natural ergot alkaloid.

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Related reactions

1 records
New reaction record
HRID 543873 reaction equation
HRID 543873As reactantuspto-grants-1984_05

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
(5'α)-12'-Hydroxy-2',5'-bis(1-Methylethyl)ergotaMan-3',6',18-trione
Ergocorine phosphateRefChem:137501DTXCID101782264209-272-7N-(2-hydroxy-5,8-dioxo-4,7-bis(propan-2-yl)-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-6-methyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),2,9,12,14-pentaene-4-carboxamideMLS000069342SMR00005893812'-hydroxy-2',5'alpha-bis(1-methylethyl)ergotaman-3',6',18-trione

Database identifiers

CAS
564-36-3
PubChem CID
73453
DTXSID
DTXSID40971841
ChEMBL
CHEMBL1385840
ChEBI
CHEBI:4820
UNII
7W36B25464
EC Number
209-272-7
Nikkaji
J14.844J
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
3
rtecs
KE7630000
ridadr
UN 1544 6.1/PG 3
hazard_class
6.1(b)
packing_group
III